Trifluoroacetic acid → (S)-4-(2-(2-carboxyacetoxy)-2-(3-(cyclopropylmethoxy)-4-(difluoromethoxy)phenyl)ethyl)-3,5-dichloropyridine 1-oxide

HRID 1776487Notes

Reaction equation

C([O:5][C:6](=[O:37])[CH2:7][C:8]([O:10][C@H:11]([C:22]1[CH:27]=[CH:26][C:25]([O:28][CH:29]([F:31])[F:30])=[C:24]([O:32][CH2:33][CH:34]2[CH2:36][CH2:35]2)[CH:23]=1)[CH2:12][C:13]1[C:18]([Cl:19])=[CH:17][N+:16]([O-:20])=[CH:15][C:14]=1[Cl:21])=[O:9])(C)(C)C.C(O)(C(F)(F)F)=O>C(Cl)Cl>[C:6]([CH2:7][C:8]([O:10][C@H:11]([C:22]1[CH:27]=[CH:26][C:25]([O:28][CH:29]([F:31])[F:30])=[C:24]([O:32][CH2:33][CH:34]2[CH2:35][CH2:36]2)[CH:23]=1)[CH2:12][C:13]1[C:18]([Cl:19])=[CH:17][N+:16]([O-:20])=[CH:15][C:14]=1[Cl:21])=[O:9])([OH:37])=[O:5]

Participants

Conditions

Temperature: 0 °C

Procedure

(S)-4-(2-(3-tert-butoxy-3-oxopropanoyloxy)-2-(3-(cyclopropylmethoxy)-4-(difluoromethoxy)phenyl)ethyl)-3,5-dichloropyridine 1-oxide (1.0561 g, 1.878 mmol) was dissolved in DCM (70 ml) and cooled to 0° C. TFA (1.447 ml, 18.78 mmol) was added slowly, and the reaction was stirred at RT for 3 days. Two more additions of TFA (0.723 ml, 9.39 mmol) were performed, and the stirring was continued overnight. The mixture was evaporated to dryness affording (S)-4-(2-(2-carboxyacetoxy)-2-(3-(cyclopropylmethoxy)-4-(difluoromethoxy)phenyl)ethyl)-3,5-dichloropyridine 1-oxide (0.950 g, 1.876 mmol, 100% yield, MS/ESI+ 505.9 [MH]+).

Workup

waitthe stirring was continued overnight
customThe mixture was evaporated to dryness

Sources & evidence

ORD record: ord-18f807bacde7477489e95fc62b978990
Source dataset: uspto-grants-2016_02
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09265768B2

Reaction notes

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